ps_3 (2) - initiation and propagation steps. What is the...

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M. Movassaghi Chemistry 5.43 Problem Set III Due in class: Monday, Mar. 12th, 2007 at 12:05 pm. In your answers, show arrow pushing and where appropriate identify initiation and propagation steps. 1. Provide a detailed mechanism for the following: O OEt t -Bu O H 3 C CH 2 CH 3 O t -Bu N O N + EtO Δ H 3 C CH 3 (mixture of diastereomers) 2. Provide a detailed mechanism for the following. Explain the stereochemical outcome including the double bond geometry? H 3 C H AIBN CH 3 CH 3 CH 3 n -Bu 3 SnH H 3 C Δ Br CH 3 (racemic) (racemic, mixture of diastereomers) H 3 C 3. Provide a detailed mechanism for the following: CH 3 O O n -Bu 3 SnH I AIBN Δ Monday 3.5.2007 4. Provide a detailed mechanism for the following. Specify the
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Unformatted text preview: initiation and propagation steps. What is the by-product X? H 3 C H AIBN + X H 3 C + CHCl 3 Δ Cl Cl (racemic, mixture of diastereomers) 5. Provide a mechanism for the formation of each of the four products. Explain the effect of concentration on the product ratios. O t-Bu O O t-Bu D D H (a) H Δ CH 3 + D D D D dilute reaction mixtures: 1 : 1 concentrated reaction mixtures: 1 : 1.5 D O t-Bu O O t-Bu D (b) CH 3 H Δ D CH 3 + dilute reaction mixtures: 1 : 1 concentrated reaction mixtures: 1 : 1.4 6. Provide a detialed mechanism for the following: CH 3 AIBN O O O O I H N n-Bu 3 SnH O CH 3 O N Δ Ph 1/1...
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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